2-triazinylacetics acid derivatives, and their use as herbicides, fungicides and plant growth regulators

ABSTRACT

The invention relates to new 2-pyrimidinyl- and 2-triazinylacetic acid derivatives of general formula I ##STR1## in which A, R 2-5  and X have the meanings given in the description, processes for their preparation and their use as herbicides, fungicides and plant growth regulants.

DESCRIPTION

This invention relates to new substituted 2-pyrimidinyl- and2-triazinylacetic acid derivatives, processes for their preparation andtheir use as herbicides, fungicides and plant growth regulators.

It is known that pyrimidine derivatives possess herbicidal activity (EP223 406, 249 707, 249 708, 287 072 and 287 079). However, the herbicidalactivity of these known compounds is often insufficient or selectivityproblems are seen in important crops.

The object of the present invention is to make new compounds that do nothave these disadvantages and have improved biological properties overthe known compounds.

It has now been found that substituted 2-pyrimidinyl- and2-triazinylacetic acid derivatives of general formula I ##STR2## inwhich A is one of the groups --CO--OR¹, --CO--NR⁶ R⁷ or --C≡N,

R¹ is hydrogen, C₁ -C₁₂ -alkyl (optionally substituted by hydroxy,halogen, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₃ -C₆ -cycloalkyl, benzyl,furyl, tetrahydrofuryl, phenyl, halophenyl, C₁ -C₄ -alkylphenyl, C₁ -C₄-alkoxyphenyl, nitrophenyl, cyano, carboxy, C₁ -C₄ -alkoxycarbonyl, C₁-C₄ -alkylamino, di-C₁ -C₄ -alkylamino, tri-C₁ -C₄ -alkylammoniumhalide,C₂ -C₅ -alkylenimino or di-C₁ -C₄ -alkylmethyleniminooxy), C₂ -C₁₂-alkyl, interrupted by one or more oxygen or sulphur atoms andoptionally substituted by hydroxy, halogen, C₁ -C₄ -alkoxy, C₁ -C₄-alkylthio, C₃ -C₆ -cycloalkyl, benzyl, furyl, tetrahydrofuryl, phenyl,halophenyl, C₁ -C₄ -alkylphenyl, C₁ -C₄ -alkoxyphenyl, nitrophenyl,cyano, carboxy, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylamino or di-C₁ -C₄-alkylamino, a C₃ -C₈ -alkenyl or C₃ -C₈ -alkynyl group (each of whichis optionally substituted by C₁ -C₃ -alkoxy, phenyl or halogen), C₃ -C₈-cycloalkyl, optionally substituted by methyl, di-C₁ -C₄-alkylmethylenimino or C₃ -C₆ -cycloalkylenimino;

R² and R³, which may be the same or different, are C₁ -C₄ -alkyl,trifluoromethyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄-alkylthio, C₁ -C₄ -alkylamino, di-C₁ -C₄ -alkylamino or halogen;

R⁴ is hydrogen, C₁ -C₁₀ -alkyl (optionally substituted by one or more ofthe same or different C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, amino, C₁ -C₄-alkylamino, di-C₁ -C₄ -alkylamino, nitro, halogen, phenyl orhalophenyl), a C₂ -C₁₀ -alkenyl or C₂ -C₁₀ -alkynyl group (each of whichis optionally substituted by one or more of the same or different C₁ -C₄-alkoxy, C₁ -C₄ -alkylthio, amino, C₁ -C₄ -alkylamino, di-C₁ -C-alkylamino, nitro, halogen or phenyl), or a C₃ -C₈ -cycloalkyl or C₄-C₈ -cycloalkenyl group (each of which is optionally substituted by oneor more of the same or different C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄-alkylthio, amino, C₁ -C₄ -alkylamino, di-C₁ -C₄ -alkylamino, nitro,trifluoromethyl, halogen or phenyl);

R⁵ has the same meaning as R⁴ except hydrogen; or

R⁴ and R⁵ together with the carbon to which they are attached form a C₃-C₈ -cycloalkyl group;

R⁶ and R⁷, which may be the same or different, are hydrogen or C₁ -C₄-alkyl;

X is methine or nitrogen,

with the provisos,

a) A is not -C≡N, when R⁴ and/or R⁵ are methyl or benzyl,

b) R¹ is not ethyl, when R⁴ is hydrogen and R⁵ is benzyl, and

c) R⁵ is not ethyl or allyl, when R¹ is hydrogen, R² and R³ are eachchlorine and X is nitrogen;

as well as their alkali metal, alkaline earth metal, ammonium andorganic ammonium salts, and their optically active isomers, showinteresting herbicidal, fungicidal and plant growth regulant activity.

The expression "halogen" means fluorine, chlorine, bromine and iodine.By the term alkali metal is meant lithium, sodium or potassium and bythe term alkaline earth metal is meant calcium, strontium or barium.

The compounds of the invention of general formula I can be prepared forexample

A) by reacting a compound of general formula II ##STR3## in which R², R³and X have the meanings given under general formula I, and Y is leavinggroup, such as halogen, alkylsulphonyl or phenylsulphonyl, with acompound of general formula III ##STR4## in which A, R⁴ and R⁵ have themeanings given under general formula I, in a suitable solvent in thepresence of a suitable base, or

B) by reacting a compound of general formula IV ##STR5## in which R¹,R², R³, R⁴, R⁵ and X have the meanings given under general formula I,except for X being hydrogen, with an alkali metal base or alkaline earthmetal base, in a suitable polar solvent, to give a compound of generalformula V ##STR6## in which R², R³, R⁴, R⁵ and X have the meanings givenunder general formula I and M¹ is an alkali metal atom or an equivalentof an alkaline earth metal atom, and optionally base, in a suitablepolar in which A, R⁴ and R⁵ have the meanings given under generalformula I, in a suitable solvent in the presence of a suitable base, or

C) by reacting a compound of general formula V ##STR7## in which R², R³,R⁴, R⁵, M¹ and X have the meanings given under general formula V, with asuitable acid, in a suitable solvent, to give a compound of generalformula VI ##STR8## in which R², R³, R⁴, R⁵ and X have the meaningsgiven under general formula I, or

D) by reacting a compound of general formula VI ##STR9## in which R²,R³, R⁴, R⁵ and X have the meanings given under general formula I, with asuitable base, in a suitable solvent, to give a compound of generalformula VII ##STR10## in which R², R³, R⁴, R⁵ and X have the meaningsgiven under general formula I and M² is an alkali metal atom or anequivalent of an alkaline earth metal atom, an ammonium ion or anorganic ammonium group, or

E) by reacting a compound of general formula VIII ##STR11## in which A,R², R³, R⁴ and X have the meanings given under general formula I, with acompound of general formula IX

    R.sup.5 --Z                                                (IX)

in which R⁵ has the meaning given under general formula I, and Z is aleaving group, such as halogen, alkylsulphonyl, phenylsulphonyl oralkoxysulphonyloxy, in a suitable solvent, in the presence of a suitablebase.

The individual process variants are preferably carried out in thepresence of a diluent. For this, a solvent which is inert to thereactants is used.

Suitable solvents include water, aliphatic, alicyclic and aromatichydrocarbons, that can be optionally chlorinated, such as for examplehexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene,methylene chloride, chloroform, carbon tetrachloride, ethylene chlorideand trichloroethane, ethers, such as for example diisopropyl ether,dibutyl ether, propylene oxide, dioxane and tetrahydrofuran; ketones,such as for example acetone, methyl ethyl ketone, methyl isopropylketone, nitriles, such as for example acetonitrile and propionitrile,alcohols, such as for example methanol, ethanol, isopropanol, butanoland ethylene glycol, esters, such as for example ethyl acetate and amylacetate, amides, such as for example dimethylformamide anddimethylacetamide, sulphones and sulphoxides, such as for exampledimethyl sulphoxide, and bases, such as for example pyridine.

The presence of a catalyst can be an advantage. Suitable catalystsinclude potassium iodide and onium compounds, such as quaternaryammonium, phosphonium and arsonium compounds as well as sulphoniumcompounds. Also suitable are polyglycol ethers, especially cyclicethers, such as 18-crown-6, and tertiary amines, such as for exampletributylamine. Preferred compounds are quaternary ammonium compounds,such as for example benzyltriethylammonium chloride andtetrabutylammonium bromide.

The reactions can be carried out under atmospheric pressure but ifdesired higher or lower pressures can be used.

The process variant A) is preferably carried out in an aprotic solventsuch as benzene, toluene, xylene, tetrahydrofuran, diethyl ether,hexane, dimethylformamide or dimethyl sulphoxide.

Bases that can be used include sodium hydride, potassium tert-butylateor lithium diisopropylamide.

The reactions are suitably carried out between -78° C. and the boilingpoint of the particular solvent or solvent mixture.

The reaction usually takes 5 minutes to 48 hours, preferably 0.5 to 24hours.

Compounds of general formula II are described in the literature or canbe prepared by methods analogous to those described in the literature.

For the processes variants B) and C), there is preferably used as asolvent an alcohol, such as ethanol, propanol or isopropanol, a ketone,such as acetone or methyl ethyl ketone, dimethylformamide or dimethylsulphoxide, water or a polar solvent/water mixture.

Bases that can be used include for example, carbonates, such as sodiumcarbonate, potassium carbonate or calcium carbonate, or metalhydroxides, such as sodium hydroxide or potassium hydroxide.

The reaction temperature lies between room temperature and the boilingpoint of the particular solvent. The reaction time lies between 0.5 to36 hours.

When R¹ in general formula IV is benzyl, a catalytic reduction(hydrogenation) of the compound of formula VI can also be used.

Suitable solvents for process variant D) include hydrocarbons, such asbenzene, toluene or xylene, halogenated hydrocarbons, such as methylenechloride or chloroform, alcohols, such as methanol, ethanol orisopropanol, ethers, such as for example diethyl ether, diisopropylether, tetrahydrofuran or 1,4-dioxane, ketones, such as acetone ormethyl ethyl ketone, esters, such as methyl acetate or ethyl acetate, ornitriles, such as acetonitrile.

Bases that can be used include an alkali metal, such as sodium orpotassium, an alkali metal or alkaline earth metal hydride, such assodium hydride, potassium hydride or calcium hydride, a carbonate, suchas sodium carbonate, potassium carbonate or calcium carbonate, or ametal hydroxide, such as sodium hydroxide or potassium hydroxide.Organic ammonium bases that can be used include for example, ammonia analkylamine (primary amine), a dialkylamine (secondary amine) or atrialkylamine (tertiary amine).

The temperature of the reaction falls within room temperature and theboiling point of the particular solvent or solvent mixture. The reactiontime lies between 5 minutes and 10 hours.

The process variant E) is preferably carried out in an aprotic solvent,such as benzene, toluene, xylene, tetrahydrofuran, diethyl ether,hexane, dimethylformamide or dimethyl sulphoxide.

Bases that can be used include for example sodium hydride, potassiumtert-butylate or lithium diisopropylamide.

The temperature of the reaction lies between -78° C. and the boilingpoint of the particular solvent or solvent mixture.

The reaction time lies between 1 and 24 hours.

The compounds of the invention prepared by these processes can beisolated from the reaction mixtures in conventional manner, for exampleby distillation of the solvent at normal or reduced pressure, byprecipitation with water or by extraction.

A higher level of purity can be achieved as a rule by columnchromatography as well as by fractional distillation or crystallisation.

The compounds of the invention are, as a rule, colourless and odourlessliquids or crystals that are soluble in water, slightly soluble inaliphatic hydrocarbons such as petroleum ether, hexane, pentane andcyclohexane and highly soluble in halogenated hydrocarbons, such aschloroform, methylene chloride and carbon tetrachloride, aromatichydrocarbons, such as benzene, toluene and xylene, ethers, such asdiethyl ether, tetrahydrofuran and dioxane, nitriles, such asacetonitrile, alcohols, such as methanol and ethanol, amides, such asdimethylformamide, and sulphoxides, such as dimethyl sulphoxide.

The compounds of the invention show a good herbicidal activity in broadleaved weeds and grasses. A selective use in various crops is possible,for example in such as rape, beets, soya beans, cotton, rice, barley,wheat and other cereals. Individual active substances are particularlysuitable as selective herbicides in beet, cotton, soya and cereals.However the compounds can be used for control of weeds in permanentcrops, such as for example forestry, ornamental trees, fruit, vine,citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruitand hop plantations and for the selective control of weeds in annualcrops.

The compounds of the invention can used for example against thefollowing plant species:

Dicotyledonous weeds of the species Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Brassica,Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Lamium, Veronica, Abutilon, Datura, Viola, Galeopsis, Papaver,Centaurea and Chrysanthemum.

Monocotyledonous weeds of the species Avena, Alopecurus, Echinochloa,Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus,Cyperus, Agropyron, Sagittaria, Monocharia, Fimbristylis, Eleocharis,Ischaemum and Apera.

The rates of use vary depending on the manner of pre- and post-emergentuse between 0.001 and 5 kg/ha.

The compounds of the invention can also be used as defoliants,desiccants and as total herbicides. They also influence plant growth andcan thus be used to influence plant growth of crops. Some compounds alsoshow fungicidal activity.

The compounds of the invention can be used either alone or in admixturewith one another or with other active agents. Optionally, otherplant-protective agents or pesticides can be added, depending on thepurpose for the treatment. When it is desired to broaden the spectrum ofactivity, other herbicides can also be added. Herbicidally active mixingpartners suitable in this connection include for example, the activeagents listed in Weed Abstracts, vol. 38, No.3 (1989) under the heading"Lists of common names and abbreviations employed for currently usedherbicides and plant growth regulators in Weed Abstracts".

An improvement in the intensity and speed of action can be obtained, forexample, by addition of suitable adjuvants, such as organic solvents,wetting agents and oils. Such additives may allow a decrease in thedose.

The designated active ingredients or their mixtures can suitably beused, for example, as powders, dusts, granules, solutions, emulsions orsuspensions, with the addition of liquid and/or solid carriers and/ordiluents and, optionally, binding, wetting, emulsifying and/ordispersing adjuvants.

Suitable liquid carriers are, for example aliphatic and aromatichydrocarbons, such as benzene, toluene, xylene, cyclohexanone,isophorone, dimethyl sulphoxide, dimethylformamide and other mineral-oilfractions and plant oils.

Suitable solid carriers include mineral earths, e.g. bentonite, silicagel, talc, kaolin, attapulgite, limestone, silicic acid and plantproducts, e.g. flours.

As surface-active agents there can be used for example calciumlignosulphonate, polyoxyethylenealkylphenyl ethers, naphthalenesulphonicacids and their salts, phenolsulphonic acids and their salts,formaldehyde condensates, fatty alcohol sulphates, as well assubstituted benzenesulphonic acids and their salts.

The percentage of the active ingredient(s) in the various preparationscan vary within wide limits. For example, the compositions can containabout 10 to 90 percent by weight active ingredients, and about 90 to 10percent by weight liquid or solid carriers, as well as, optionally up to20 percent by weight of surfactant.

The agents can be applied in customary fashion, for example with wateras the carrier in spray mixture volumes of approximately 100 to 1,000l/ha. The agents can be applied using low-volume or ultra-low-volumetechniques or in the form of so-called microgranules.

The preparation of these formulations can be carried out in knownmanner, for example by milling or mixing processes. Optionally,individual components can be mixed just before use for example by theso-called commonly used tank-mixing method.

Formulations can be prepared, for example, from the followingingredients.

A) Wettable Powder

1)

25 percent by weight active ingredient

60 percent by weight kaolin

10 percent by weight silicic acid

5 percent by weight of a mixture of calcium lignosulphonate and thesodium salt of N-methyl-N-oleyltaurine

2)

40 percent by weight active ingredient

25 percent by weight bentonite

25 percent by weight colloidal silicic acid

10 percent by weight of a mixture of calcium lignosulphonate andalkylphenyl polyglycol ether

B) Paste

45 percent by weight active ingredient

5 percent by weight sodium aluminium silicate

15 percent by weight cetyl polyglycol ether with 8 mol of ethylene oxide

2 percent by weight spindle oil

10 percent by weight polyethylene glycol

23 percent by weight water

C) Emulsifiable Concentrate

25 percent by weight active ingredient

15 percent by weight cyclohexanone

55 percent by weight xylene

5 percent by weight of a mixture of calcium dodecylbenzenesulphonate andnonylphenolpolyoxyethylene.

The following Examples illustrate the preparation of compounds of theinvention.

EXAMPLE 1 Ethyl 2-(4,6-dimethoxypyrimidin-2-yl)pentanoate

4,2 g (30 mmol) Diisopropylamine in 100 ml tetrahydrofuran, undernitrogen at -78° C., was treated with 19 ml (30 mmol) 1.6M butyllithiumin hexane. The mixture was stirred for 30 minutes and then at -60° C., asolution of 3.5 g (27 mmol) ethyl pentanoate, dissolved in 20 mltetrahydrofuran, was added dropwise. The mixture was stirred for afurther hour and 5.9 g (27 mmol)4,6-dimethoxy-2-methylsulphonylpyrimidine was added, portionwise. Thetemperature of the mixture rose over 2 hours to +10° C. The reactionmixture was then washed with saturated aqueous ammonium chloride andsodium chloride. The aqueous phase was extracted with ethyl acetate. Theorganic phases were dried over magnesium sulphate and concentrated. Theresulting yellow oil was finally purified on silica gel using ahexane/ethyl acetate mixture (0 to 20% ethyl acetate).

Yield: 3.2 g=42% of theory

n²⁰ _(D) : 1.4824

EXAMPLE 2 2-(4,6-Dimethoxypyrimidin-2-yl)pentanoic acid

A mixture of 2.2 g (8 mmol) ethyl2-(4,6-dimethoxypyrimidin-2-yl)pentanoate in 20 ml methanol and 3 ml 5Ncaustic soda was stirred overnight at room temperature. The mixture wasconcentrated and the residue dissolved in 10 ml water, extracted with 50ml ethyl acetate and the aqueous phase acidified with 2N hydrochloricacid until it was pH 5. The aqueous phase was extracted three times withether, the combined phases were dried over magnesium sulphate andconcentrated.

Yield: 1.7 g=85% of theory

mp: 71-73° C. (dec.)

EXAMPLE 3 Methyl 2,4-dimethyl-2-(4,6-dimethoxy-s-triazin-2-yl)pentanoate

0.5 g (17 mmol) Sodium hydride (80% in oil) was added at roomtemperature, under nitrogen, to a solution of 3.96 g (14 mmol) methyl2-(4,6-dimethoxy-s-triazin-2-yl)pentanoate in 35 ml dimethylformamide.The mixture was stirred for one hour at room temperature and then 2.0 g(16 mmol) dimethyl sulphate was added dropwise. The mixture was left for2.5 hours at room temperature, then added to 200 ml water and extractedtwice with ethyl acetate. The combined organic phase was washed withsaturated aqueous sodium chloride, dried over magnesium sulphate andconcentrated. The crude product was purified by silica gelchromatography using a hexane/ethyl acetate mixture (0 to 20% ethylacetate).

Yield: 2.3 g=62% of theory

n²⁰ _(D) : 1.4775

In a similar manner the following compounds were prepared

    __________________________________________________________________________     ##STR12##                                                                    Ex-                                                                           am-                                                                           ple                                                    Physical               No R.sup.1        R.sup.2                                                                              R.sup.3                                                                              R.sup.4  R.sup.5    X  constant               __________________________________________________________________________     4 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4794                  5 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH mp:                                                                           109-110°                                                               C.                                                                            (dec.)                  6 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        Cyclohexyl CH n.sub.D.sup.20 :                                                              1.5028                  7 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        Cyclohexyl CH n.sub.D.sup.20 :                                                              1.4982                  8 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        Cyclohexyl CH mp: 88-89°                                                             C.                                                                            (dec.)                  9 CH.sub.3       OCH.sub. 3                                                                           OCH.sub.3                                                                            H        C(CH.sub.3).sub.3                                                                        CH n.sub.D.sup.20 :                                                              1.4868                 10 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.4 CH.sub.3                                                                CH n.sub.D.sup.20 :                                                              1.4755                 11 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.4 CH.sub.3                                                                CH n.sub.D.sup.20 :                                                              1.4920                 12 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.2 SCH.sub.3                                                               CH n.sub.D.sup.20 :                                                              1.5175                 13 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.2 CH(CH.sub.3).sub.2                                                              CH n.sub.D.sup.20 :                                                              1.4773                 14 CH.sub.2 CH.sub.3                                                                            Cl     OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4926                 15 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4796                 16 CH.sub.2 CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4803                 17 CH.sub.2 CH.sub.3                                                                            CH.sub.3                                                                             CF.sub.3                                                                             H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4406                 18 CH.sub.2 CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4794                 19 CH.sub.3       OCH.sub. 3                                                                           OCH.sub.3                                                                            CH.sub.3 (CH.sub.2).sub.2 CH.sub.3                                                                CH n.sub.D.sup.20 :                                                              1.4829                 20 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.2 CH(CH.sub.3).sub.2                                                              N  n.sub.D.sup.20 :                                                              1.4740                 21 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.3   CH n.sub.D.sup.20 :                                                              1.4808                 22 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2)CH.sub.3                                                                       CH n.sub.D.sup.20 :                                                              1.4834                 23 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4834                 24 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        C(CH.sub.3).sub.3                                                                        N  mp: 82-83°                                                             C.                                                                            (dec.)                 25 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.2 CHCH.sub.2                                                                      N  n.sub.D.sup.20 :                                                              1.4966                 26 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.2 CHCH.sub.2                                                                      N  n.sub.D.sup.20 :                                                              1.4882                 27 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.2 CHCH.sub.2                                                                      N  mp: 71-73°                                                             C.                     28 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.2 CH(CH.sub.3).sub.2                                                              N  mp: 86-88°                                                             C.                     29 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.2 CCH                                                                     N  n.sub.D.sup.20 :                                                              1.4903                 30 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.2 CCH                                                                     N  mp: 73-75°                                                             C.                                                                            (dec.)                 31 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4815                 32 CH.sub.2 (CH.sub.3).sub.2                                                                    OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4744                 33 Tetrahydrofurfuryl                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4946                 34 CH.sub.2 CCH   OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4922                 35 CH.sub.2 CHC(CH.sub.3)CCH                                                                    OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.5021                 36 H.sub.3 NCH(CH.sub.2).sub.2                                                                  OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  mp: 127°                                                               C.                                                                            (dec.)                 37 NC(CH.sub.3).sub.2                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4895                 38 CH.sub.2 OCH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4782                 39 CH.sub.2 CCH   OCH.sub.3                                                                            OCH.sub.3                                                                            H        C(CH.sub.3).sub.3                                                                        N  mp: 72-74°                                                             C.                                                                            (dec.)                 40 CH.sub.2 CHC(CH.sub.3)CCH                                                                    OCH.sub.3                                                                            OCH.sub.3                                                                            H        C(CH.sub.3).sub.3                                                                        N  n.sub.D.sup.20 :                                                              1.5049                 41 CH.sub.3       OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                    H        CH(CH.sub.3).sub.2                                                                       N  mp: 46° C.      42 CH.sub.3       CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4805                 43 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            (CH.sub.2).sub.5    CH n.sub.D.sup.20 :                                                              1.5056                 44 H              OCH.sub.3                                                                            OCH.sub.3                                                                            (CH.sub.2).sub.5    CH mp: 88-90°                                                             C.                     45 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            (CH.sub.2).sub.3    CH n.sub.D.sup.20 :                                                              1.4928                 46 H              OCH.sub.3                                                                            OCH.sub.3                                                                            (CH.sub.2).sub.3    CH mp:                                                                           120-121°                                                               C.                                                                            (dec.)                 47 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.2CHCH.sub.2                                                                     CH.sub.2 CH(CH.sub.3).sub.2                                                              N  n.sub.D.sup.20 :                                                              1.4856                 48 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.3 CH.sub.3                                                                N  n.sub.D.sup.20 :                                                              1.4716                 49 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.2 CH(CH.sub.3).sub.2                                                              N  n.sub.D.sup.20 :                                                              1.4794                 50 H              OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3 (CH.sub.2).sub.2 CH.sub.3                                                                CH mp: 68-70°                                                             C.                     51 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3 CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4813                 52 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3 CH.sub.2 CHCH.sub.2                                                                      CH n.sub.D.sup.20 :                                                              1.4884                 53 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.3 CH.sub.                                                                 CH n.sub.D.sup.20 :                                                              1.3769                 54 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.3 CH.sub.3                                                                CH n.sub.D.sup.20 :                                                              1.4781                 55 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.3 CH.sub.3                                                                CH mp: 71-72°                                                             C.                     56 NC(CH.sub.3).sub.2                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.3 CH.sub.3                                                                CH n.sub.D.sup.20 :                                                              1.4972                 57 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.2CCH                                                                            CH.sub.2 CCH                                                                             CH mp: 70-73°                                                             C.                     58 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.2 CH.sub.3                                                                N  n.sub.D.sup.20 :                                                              1.4844                 59 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        Cyclopropylmethyl                                                                        CH n.sub.D.sup.20 :                                                              1.4973                 60 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3)CH.sub.2 CH.sub.3                                                            CH n.sub.D.sup.20 :                                                              1.4846                 61 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3)CH.sub.2 CH.sub.3                                                            CH n.sub.D.sup.20 :                                                              1.4796                 62 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3) CH.sub.2 CH.sub.3                                                           N  n.sub.D.sup.20 :                                                              1.4864                 63 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3)CH.sub.2 CH.sub.3                                                            N  n.sub.D.sup.20 :                                                              1.4777                 64 Tetrahydrofurfuryl                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.3 CH.sub.2                                                              N  n.sub.D.sup.20 :                                                              1.4903                 65 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.3   CH mp: 79° C.                                                             (dec.)                 66 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.2 CH.sub.3                                                                        CH n.sub.D.sup.20 :                                                              1.4816                 67 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.2 CH.sub.3                                                                        CH n.sub.D.sup.20 :                                                              1.4807                 68 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3)CH.sub.2 CH.sub.3                                                            CH mp: 82° C.                                                             (dec.)                 69 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.2 CH.sub.3                                                                        CH mp: 97° C.                                                             (dec.)                 70 NC(CH.sub.3).sub.2                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3)CH.sub.2 CH.sub.3                                                            CH mp: 124°                                                               C.                                                                            (dec.)                 71 NC(CH.sub.3 ).sub.2                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.2 CH.sub.3                                                                CH n.sub.D.sup.20 :                                                              1.4974                 72 NC(CH.sub.3)CH.sub.2 CH.sub.3                                                                OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4946                 73 Benzyl         OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.5226                 74 Benzyl         OCH.sub.3                                                                            Cl     H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.5351                 75 (CH.sub.2).sub.2 ONC(CH.sub.3).sub.2                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4852                 76 CH.sub.2 CH.sub.3                                                                            OCH.sub.2 CH.sub.3                                                                   OCH.sub.2 CH.sub.3                                                                   H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4758                 77 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            Cl     H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4891                 78 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            (CH.sub.2).sub.3 CH.sub.3                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4685                 79 (CH.sub.2).sub.2N(CH.sub.3).sub.2                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4850                 80 (CH.sub.2).sub.2N(CH.sub.2 ).sub.5                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4967                 81 (CH.sub.2).sub.3 CH.sub.3                                                                    OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4763                 82 (CH.sub.2).sub.2 OCH.sub.2 CH.sub.3                                                          OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4755                 83 (CH.sub.2).sub.2 O(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3                                        OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4759                 84 (CH.sub.2).sub.2 Obenzyl                                                                     OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.5166                 85 (CH.sub.2).sub.2 OH                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4972                 86 CH.sub.2 CO.sub.2 H                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N                         87 CH.sub.2 CO.sub.2 CH.sub.3                                                                   OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N                         88 H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        1-Methylbenzyl                                                                           CH mp: 141°                                                               C.                                                                            (dec.)                 89 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        1-Methylbenzyl                                                                           CH mp: 81° C.      90 CH.sub.2 CH.sub.3                                                                            OCH.sub.2 CH.sub.3                                                                   OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4732                 91 CH.sub.2 CO.sub.2 CH.sub.3                                                                   OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4859                 92 CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4809                 93 (CH.sub.2).sub.2N(CH.sub.3).sub.3                                                            OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  mp: 74-76°                                                             C.                     94 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.2 CH.sub.3                                                                   H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4746                 95 CH.sub.2 CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4773                 96 CH.sub.2 CH.sub.3                                                                            OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                                                                  H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4724                 97 CH.sub.2 CH.sub.3                                                                            OCH(CH.sub.3).sub.2                                                                  OCH(CH.sub.3).sub.2                                                                  H        CH(CH.sub.3).sub.2                                                                       N  n.sub.D.sup.20 :                                                              1.4688                 98 CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        Benzyl     CH n.sub.D.sup.24 :                                                              1.5350                 99 CH.sub. 3      OCH.sub.3                                                                            OCH.sub.3                                                                            Benzyl   Benzyl     CH mp:                                                                           107-109°                                                               C.                     100                                                                              H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        Benzyl     CH mp:                                                                           100-104°                                                               C.                     101                                                                              CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            3-Chlorobenzyl                                                                         3-Chlorobenzyl                                                                           CH n.sub.D.sup.24 :                                                              1.5660                 102                                                                              CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        3-Chlorobenzyl                                                                           CH n.sub.D.sup.24 :                                                              1.5410                 103                                                                              CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            4-Chloro-benzyl                                                                        4-Chloro-benzyl                                                                          CH mp:                                                                           122-125°                                                               C.                     104                                                                              H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        3-Chlorobenzyl                                                                           CH mp:                                                                           117-118°                                                               C.                     105                                                                              CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        4-Chlorobenzyl                                                                           CH mp: 66-68°                                                             C.                     106                                                                              H              OCH.sub.3                                                                            OCH.sub.3                                                                            H        4-Chlorobenzyl                                                                           CH mp:                                                                           103-104°                                                               C.                     107                                                                              CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            (CH.sub.2).sub.3 CH.sub.3                                                              (CH.sub.2).sub.3 CH.sub.3                                                                CH n.sub.D.sup.24 :                                                              1.4780                 108                                                                              CH.sub.3       OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH.sub.2 CCH                                                                             CH n.sub.D.sup.24 :                                                              1.5020                 109                                                                              (CH.sub.2).sub.3CO.sub.2 CH.sub.2 CH.sub.3                                                   OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup. 20 :                                                             1.4768                 __________________________________________________________________________     ##STR13##                                                                    Ex-                                                                           am-                                                                           ple                                                    Physical               No A              R.sup.2                                                                              R.sup.3                                                                              R.sup.4  R.sup.5    X  constant               __________________________________________________________________________    110                                                                              CN             OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4930                 111                                                                              CONH.sub.2     OCH.sub.3                                                                            OCH.sub.3                                                                            H        (CH.sub.2).sub.3 CH.sub.3                                                                CH mp: 75-76°                                                             C.                     112                                                                              CONH.sub.2     OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH mp:                                                                           103-105°                                                               C.                     113                                                                              CON(CH.sub.3).sub.2                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.5030                 114                                                                              CON(C.sub.2 H.sub.5).sub.2                                                                   OCH.sub.3                                                                            OCH.sub.3                                                                            H        CH(CH.sub.3).sub.2                                                                       CH n.sub.D.sup.20 :                                                              1.4960                 __________________________________________________________________________

The following examples illustrate the possibilities for use of thecompounds of the invention.

EXAMPLE A

In a greenhouse, the noted plant species were treated pre-emergentlywith the noted compounds of the invention, at a rate of 0.3 kg activeingredient/ha. The compounds of the invention were sprayed evenly overthe soil as emulsions or suspensions in 500 liters water/ha. Three weeksafter the treatment, the compounds of the invention showed excellentactivity against the weeds. The comparison material did not show similarhigh efficacy.

In the following table:

    __________________________________________________________________________               0 = no damage                                                                 1 = 1-24% damage                                                              2 = 25-74% damage                                                             3 = 75-89% damage                                                             4 = 90-100% damage                                                            AGRRE = Elymus repens                                                         BROTE = Bromus tectorum                                                       SORHA = Sorghum halepense                                                     ABUTH = Abutilon theophrasti                                                  IPOSS = Ipomoea purpurea                                                      SEBEX = Sesbania exaltata                                          __________________________________________________________________________    Compound                                                                      of the invention                                                                       AGRRE                                                                              BROTE                                                                              SORHA                                                                              ABUTH                                                                              IPOSS                                                                             SEBEX                                        __________________________________________________________________________    Example 5                                                                              3    4    3    3    3   3                                            Example 15                                                                             3    4    3    3    3   3                                            Example 23                                                                             3    4    3    --   3   3                                            Example 33                                                                             3    3    3    2    2   2                                            Example 36                                                                             3    4    4    3    2   3                                            Example 62                                                                             3    4    3    --   --  2                                            Example 63                                                                             3    3    3    3    --  3                                            Example 64                                                                             3    3    3    3    2   3                                            Example 70                                                                             3    4    3    4    3   3                                            Example 72                                                                             3    4    3    3    2   3                                            Example 73                                                                             3    4    3    4    2   3                                            Untreated                                                                              0    0    0    0    0   0                                            Comparison                                                                    Imazamethabenz                                                                         1    2    2    2    2   1                                            __________________________________________________________________________

EXAMPLE B

In a greenhouse, the noted plant species were treated post-emergentlywith the noted compounds of the invention, at a rate of 0.1 kg activeingredient/ha. The compounds of the invention were sprayed evenly overthe plants as emulsions or suspensions in 500 liters water/ha. Two weeksafter the treatment, the compounds of the invention showed a high cropselectivity in wheat and maize with excellent activity against theweeds. The comparison material did not show similar high efficacy.

In the following table:

    __________________________________________________________________________                     0 = no damage                                                                 1 = 1-24% damage                                                              2 = 25-74% damage                                                             3 = 75-89% damage                                                             4 = 90-100% damage                                                            GLMXA = Glycine maxima                                                        GOSHI = Gossypium hersutum                                                    HELAN = Helianthus annuus                                                     TRZAX = Triticum aestivum                                                     BROTE = Bromus tectorum                                                       GALAP = Galium aparine                                                        VERPE = Veronica persica                                                      VIOSS = Viola sp                                             __________________________________________________________________________    Compound                                                                      of the invention                                                                       GLMXA                                                                              GOSHI                                                                              HELAN                                                                              TRZAX                                                                              BROTE                                                                              GALAP                                                                              VERPE                                                                              VIOSS                             __________________________________________________________________________    Example 5                                                                              0    0    0    1    3    3    3    3                                 Untreated                                                                              0    0    0    0    0    0    0    0                                 Comparison                                                                    Imazamethabenz                                                                         0    1    1    0    0    1    2    1                                 __________________________________________________________________________

EXAMPLE C

In a greenhouse, the noted plant species were treated pre-emergentlywith the noted compounds of the invention, at a rate of 0.3 kg activeingredient/ha. The compounds of the invention were sprayed evenly overthe soil as emulsions or suspensions in 500 liters water/ha. Three weeksafter the treatment, the compounds of the invention showed excellentactivity against the weeds. The comparison material did not show similarhigh efficacy.

In the following table:

    ______________________________________                                                0 = no damage                                                                 1 = 1-24% damage                                                              2 = 25-74% damage                                                             3 = 75-89% damage                                                             4 = 90-100% damage                                                            GLMXA = Glycine maxima                                                        GOSHI = Gossypium hirsutum                                                    HELAN = Helianthus annuus                                                     BROTE = Bromus tectorum                                                       PANSS = Panicum maximum                                               ______________________________________                                        Compound                                                                      of the                                                                        invention                                                                             GLXMA    GOSHI    HELAN  BROTE  PANSS                                 ______________________________________                                        Example 4                                                                             0        0        0      3      3                                     Example 8                                                                             1        1        1      3      3                                     Example 20                                                                            1        --       0      3      3                                     Example 31                                                                            0        0        1      3      3                                     Example 32                                                                            0        1        1      --     3                                     Example 34                                                                            0        --       1      3      3                                     Example 35                                                                            0        --       0      3      3                                     Example 37                                                                            0        0        0      3      3                                     Example 38                                                                            --       --       1      3      3                                     Example 60                                                                            1        0        0      3      3                                     Example 61                                                                            0        0        0      3      3                                     Example 68                                                                            1        1        1      --     3                                     Example 71                                                                            --       1        1      3      3                                     Example 75                                                                            0        --       1      3      3                                     Untreated                                                                             0        0        0      0      0                                     Com-                                                                          parison                                                                       Imazameth-                                                                            1        0        0      0      1                                     abenz                                                                         ______________________________________                                    

EXAMPLE D

In a greenhouse, the noted plant species were treated pre-emergentlywith the noted compounds of the invention, at a rate of 0.1 kg activeingredient/ha. The compounds of the invention were sprayed evenly overthe soil as emulsions or suspensions in 500 liters water/ha. Three weeksafter the treatment, the compounds of the invention showed excellentactivity against the weeds. The comparison material did not show similarhigh efficacy.

In the following table:

    ______________________________________                                                0 = no damage                                                                 1 = 1-24% damage                                                              2 = 25-74% damage                                                             3 = 75-89% damage                                                             4 = 90-100% damage                                                            TRZAX = Triticum aestivum                                                     VERPE = Veronica persica                                                      VIOSS = Viola sp                                                      ______________________________________                                        Compound                                                                      of the invention                                                                           TRZAX      VERPE    VIOSS                                        ______________________________________                                        Example 22   0          3        3                                            Untreated    0          0        0                                            Comparison                                                                    Imazamethabenz                                                                             0          1        2                                            ______________________________________                                    

EXAMPLE E

In a greenhouse, the noted plant species were treated pre-emergentlywith the noted compounds of the invention, at a rate of 1.0 kg activeingredient/ha. The compounds of the invention were sprayed evenly overthe soil as emulsions or suspensions in 500 liters water/ha. Three weeksafter the treatment, the compounds of the invention showed excellentactivity against the weeds. The comparison material did not show similarhigh efficacy.

In the following table:

    __________________________________________________________________________                     0 = no damage                                                                 1 = 1-24% damage                                                              2 = 25-74% damage                                                             3 = 75-89% damage                                                             4 = 90-100% damage                                                            GLMXA = Glycine maxima                                                        GOSHI = Gossypium hersutum                                                    ZEAMX = Zea mays                                                              BROTE = Bromus tectorum                                                       SETVI = Setaria viridis                                                       GALAP = Galium aparine                                                        MATCH = Matricaria chamomilla                                                 VERPE = Veronica persica                                                      VIOSS = Viola sp                                             __________________________________________________________________________    Compound                                                                      of the invention                                                                       GLXMA                                                                              GOSHI                                                                              ZEAMX                                                                              BROTE                                                                              SETVI                                                                             GALAP                                                                              MATCH                                                                              VERPE                                                                              VIOSS                         __________________________________________________________________________    Example 24                                                                             0    0    0    3    3   3    3    3    3                             Example 59                                                                             0    1    --   --   3   3    --   3    3                             Example 67                                                                             1    0    1    3    --  3    --   3    3                             Untreated                                                                              0    0    0    0    0   0    0    0    0                             Comparison                                                                    Imazamethabenz                                                                         3    2    2    2    3   3    3    3    3                             __________________________________________________________________________

We claim
 1. Substituted 2-triazinylacetic acid derivative of formula I##STR14## in which A is one of the groups --CO--OR¹ or --CO--NR⁶ R⁷,R¹is hydrogen, C₁ -C₁₂ -alkyl (optionally substituted by hydroxy, halogen,C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₃ -C₆ -cycloalkyl, benzyl, furyl,tetrahydrofuryl, phenyl, halophenyl, C₁ -C₄ -alkylphenyl, C₁ -C₄-alkoxyphenyl, nitrophenyl, cyano, carboxy, C₁ -C₄ -alkoxycarbonyl, C₁-C₄ -alkylamino, di-C₁ -C₄ -alkylamino, tri-C₁ -C₄ -alkylammoniumhalide,C₂ -C₅ -alkylenimino or di-C₁ -C₄ -alkylmethyleniminooxy), C₂ -C₁₂-alkyl, interrupted by one or more oxygen or sulphur atoms andoptionally substituted by hydroxy, halogen, C₁ -C₄ -alkoxy, C₁ -C₄-alkylthio, C₃ -C₆ -cycloalkyl, benzyl, furyl, tetrahydrofuryl, phenyl,halophenyl, C₁ -C₄ -alkylphenyl, C₁ -C₄ -alkoxyphenyl, nitrophenyl,cyano, carboxy, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylamino or di-C₁ -C₄-alkylamino, a C₃ -C₈ -alkenyl or C₃ -C₈ -alkynyl group (each of whichis optionally substituted by C₁ -C₄ -alkoxy, phenyl or halogen), C₃ -C₈-cycloalkyl, optionally substituted by methyl, di-C₁ -C₄-alkylmethylenimino or C₃ -C₆ -cycloalkylenimino; R² and R³, which maybe the same or different, are C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄-alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio, C₁ -C₄-alkylamino, di-C₁ -C₄ -alkylamino or halogen; R⁴ is hydrogen, C₁ -C₁₀-alkyl (optionally substituted by one or more of the same or differentC₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, amino, C₁ -C₄ -alkylamino, di-C₁ -C₄-alkylamino, nitro, halogen, phenyl or halophenyl), a C₂ -C₁₀ -alkenylor C₂ -C₁₀ -alkynyl group (each of which is optionally substituted byone or more of the same or different C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio,amino, C₁ -C₄ -alkylamino, di-C₁ -C₄ -alkylamino, nitro, halogen orphenyl), or a C₃ -C₈ -cycloalkyl or C₄ -C₈ -cycloalkenyl group (each ofwhich is optionally substituted by one or more of the same or differentC₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, amino, C₁ -C₄-alkylamino, di-C₁ -C₄ -alkylamino, nitro, trifluoromethyl, halogen orphenyl); R⁵ has the same meaning as R⁴ except hydrogen; or R⁴ and R⁵together with the carbon to which they are attached form a C₃ -C₈-cycloalkyl group; R⁶ and R⁷, which may be the same or different, arehydrogen or C₁ -C₄ -alkyl; X is nitrogen,with the provisos, a) R¹ is notethyl, when R⁴ is hydrogen and R⁵ is benzyl, and b) R⁵ is not ethyl orallyl, when R¹ is hydrogen, and R² and R³ are each chlorine;as well astheir alkali metal, alkaline earth metal, ammonium and organic ammoniumsalts, and their optically active isomers.
 2. A herbicidal compositionwhich comprises a herbicidal effective amount of a compound according toclaim 1, in admixture with agriculturally acceptable carriers ordiluents.
 3. A method of combating weeds which comprises applying to theweeds or their locus a herbicidally effective amount of a compoundaccording to claim
 1. 4. Derivative according to claim 1 in which R² andR³ are alkoxy, R⁴ is hydrogen and A is CO₂ R¹.
 5. Derivative accordingto claim 4 in which R⁵ is alkyl and R¹ is hydrogen, alkyl, furylalkyl,alkenyl, alkynyl, benzyl or dialkylmethylimino.
 6. Derivative accordingto claim 5 in which R¹ is alkyl.
 7. Derivative according to claim 6 inwhich R¹ contains 1, 2 or 3 carbon atoms and R⁵ contains 3 or 4 carbonatoms.
 8. Derivative according to claim 7 in which R¹ is ethyl and R⁵ isisopropyl.
 9. A herbicidal composition which comprises a herbicidaleffective amount of a compound according to claim 4, in admixture withagriculturally acceptable carriers or diluents.
 10. A herbicidalcomposition which comprises a herbicidal effective amount of a compoundaccording to claim 5, in admixture with agriculturally acceptablecarriers or diluents.
 11. A herbicidal composition which comprises aherbicidal effective amount of a compound according to claim 6, inadmixture with agriculturally acceptable carriers or diluents.
 12. Aherbicidal composition which comprises a herbicidal effective amount ofa compound according to claim 7, in admixture with agriculturallyacceptable carriers or diluents.
 13. A herbicidal composition whichcomprises a herbicidal effective amount of a compound according to claim8, in admixture with agriculturally acceptable carriers or diluents. 14.A method of combating weeds which comprises applying to the weeds ortheir locus a herbicidally effective amount of a compound according toclaim
 4. 15. A method of combating weeds which comprises applying to theweeds or their locus a herbicidally effective amount of a compoundaccording to claim
 5. 16. A method of combating weeds which comprisesapplying to the weeds or their locus a herbicidally effective amount ofa compound according to claim
 6. 17. A method of combating weeds whichcomprises applying to the weeds or their locus a herbicidally effectiveamount of a compound according to claim
 7. 18. A method of combatingweeds which comprises applying to the weeds or their locus aherbicidally effective amount of a compound according to claim 8.